Jack's ex, Jack's slave Ch. 03

Jack and his slut drove back to his apartment without talking. When they had parked in the garage, Jack told her to get out and get her dress on. She stepped out of the SUV and opened the back seat. She couldn't see her dress in the back.

"Ummm, master? I don't see my dress in the back seat."

"That's because I have in my hands." Jack had stepped out and already started heading to the elevator. She shut the door and rushed to catch up, but not before an older man who had just got out of his car noticed her running by. He was exposed to the wonderful sight of a set of natural 32D breasts, bouncing along on her chest, and a good view of her round bubble butt as she ran past. He couldn't help it, and he whistled his approval.

She stopped and turned. She hadn't noticed him standing there. She didn't realize, but she was now exposing all her forward assets to him, and she saw his eyes travel from her head to her feet and back up. He smiled lecherously:

"Hey babe, I think you forgot something."

She went a deep shade of red, turned, and ran to the elevator. Her master had just stepped in and she didn't want to be stuck down here alone with the man. She just got inside as the doors closed. He threw her dress at her feet.

She bent down and put it on, as the elevator kept rising. She had just tied it, when the elevator opened on Jack's floor.

"Take off the dress."

She was confused. She had just finished putting it on. He stepped out of the elevator and turned to look at her.

"That's hesitation. Would you like to make it disobedience?"

She quickly stepped off the elevator and untied her dress. As she was pulling it off her arms, a door opened behind her. She heard it, but didn't dare turn to look. Jack had a very angry look on his face... And she didn't want to make her punishment any worse then it already was. He turned and walked to his door. She resigned herself, removed it and walked to the door. She walked in and closed it behind her.

Although she was relieved that she was in the privacy of his apartment, she was also wet enough to fill a pool. The effect of the alcohol from earlier and the fact that at least 2 people in the building had seen her naked had her turned on like never before. She was leaning against the door, on the inside, and her breathing was speeding up. Jack hasn't said anything since he came in. In fact, she didn't see him. She headed to the living room and didn't see him so assumed he would be in the bedroom.

When she walked in, she found him pulling out a toolbox. He opened it and removed a drill, a hammer and some other tools she couldn't identify.

"I'm heading downstairs to get the bags. Sit down and relax. I'll be back in a couple of minutes."

"Thank you, master. I will."

Jack figured she would be way too horny to resist taking care of herself. He was planning on catching her in the act, so he hurried downstairs, grabbed all the bags, including his purchases from the sex shop, and headed up.

He was gone about 5 minutes total, so knew she would be either very close to a first cum, or in the process of building up to a second orgasm.

He opened the door slowly, and as expected, found her on the sofa, legs spread and two fingers pistoning in and out of her sloppy cunt. She was so wet you could hear the sound her pussy was making.

Her eyes were closed, and judging by her breathing she was close to her release. He dropped the bags loudly and shouted at her:

"Slut, did I give you permission to play with yourself?"

The look on her face was priceless. Jack almost laughed out when he saw it. He contained himself and continued:

"You are going to have to be taught a pretty severe lesson tonight. It's too bad, I had something special planned for you.

"But due to your hesitation downstairs and now this... Well, it's going to be special for a different reason."

He smiled, trying to make it look evil. She still hadn't removed her fingers but had stopped moving them. Looked like whatever she had built up to was now on hold, fear having taken over.

"Cunt, don't just sit there. Squat like I taught you last night."

She quickly got into position. She just sat there, pussy spread open as shown, and waited.

Jack put the clothing bags away and grabbed the tools. He spent about half an hour installing the hooks and straps and various hardware he bought from the sex shop in the bedroom.

She could hear him working in the other room. Her legs were hurting, and her pussy was feeling pretty cold since her lips were spread and she hadn't stopped creaming.

Jack finally came back into the living room. He grabbed her by the hair and forced her forward. She stuck out her arms and he dragged her on all fours into his bedroom. Her legs were in pretty serious pain from the squatting and were cramping while she was on all fours. Once in the room, she noticed a few straps around the bed and some hooks on the ceiling and walls. She wondered what they were all for.

He pulled up on her hair, indicating he wanted her to stand up. The pain started slowly dissipating from her knees and ankles as she got to her feet.

Jack was going to test her limits. He wasn't planning on causing any long term damage, but he wouldn't stop for some light bruising this time. He grabbed some rope and got started.

He placed her in the centre of the room, at the foot of the bed. Then, he spread her legs and secured them to the feet at the corners. Next, he bent her slightly forward and stretched her arms out to the side. He had affixed hooks into the ceiling, about 2 feet in from the foot of the bed and drew the ropes trough them and tied them off.

She was now secured, her shins against the edge of the mattress, he body angled 45 degrees forward and arms raised in the air and forward.

He had considered this position specifically because her tits would be hanging down, her head would be aiming up, and her ass would be sticking out. For what he wanted to do this evening, these were important factors.

He pulled out a bunch of items from his bag, and the Cunt was wondering what all these things were. He placed the objects at the foot of the bed. He then grabbed a red ball with some straps attached and placed it in her mouth. He attached the leather belt behind her head, making sure it was secure.

Next, he took a rope and attached it to the buckle, pulling her head back and attaching it to a hook in the ceiling. Now he could only look forward, and not see what he would be doing to her body.

"Slut, I want you to know a few things before we get started.

"A year and a half ago, you left me, despite our time together, without any warning or any attempt to work on our troubles.

"Although it left me heartbroken, I tried my best to become a better person and try and win you back.

"When I realized it wasn't going to work, I decided to move. Just over a year ago, you and I met so I could let you know I was leaving. You happily informed me you were also moving, in with the other guy.

"Well, at that point, all the love I had for you and hope for us became anger.

"I want to hurt you, and I will. And to make sure that no one comes knocking on our door, I have placed a the nice red rubber ball in your mouth. Another reason I have decided to gag you is so I don't have to listen to you beg me to stop. You will be subjected to all of this, no mercy will be granted.

"So, lets get started."

She was panicking. She was starting to have doubts. Maybe this wasn't what she wanted. She expected to be disciplined, some light bondage, maybe some spanking. Everything thus far was perfectly acceptable to her.

But now? He wanted to hurt her for the sake of hurting her. Was she wrong about him? Did she underestimate his feelings since the breakup? All these these questions were going through her mind when she felt a sharp pain at her left nipple, and she couldn't tilt her head down to see what was causing it.

Jack had just attached a clothespin to her left nipple. Then he attached another to her right nub. He had also tied one end of some thin rope to the pins. He then proceeded to attach more pins, all around her areoles, in an extending spiral till he had reached the outside of her tits.

She couldn't see what was happening, but the pain was immense. Every second, another sharp pinching pain would hit her from her tits. It was working its way out, from the middle. And what's worse, the sharp sting was followed by a consistent pain in every spot. She figured he was attaching something to her skin, most likely pins. He had tried to convince her in the past, but she didn't want to have any marks or bruises on her skin. Now, it felt like hundreds of them were all over her breasts.

He had threaded the rope through the 20 or so pins on each breast. Then, he brought both ends together and ran a single line of pins from the top of her stomach till just above her pussy.

Now came the critical part. He inserted a finger in her pussy and slowly stroked the spongy pad at the roof of her cunt. He wanted her wet and distracted. After about a minute of this slow pace, he pulled out and used the wetness on his finger to rub her clit. He stroked it for over 2 minutes. In that time, her breathing had sped up, her skin was getting rosy, and she was starting to glow from perspiration. He figured he wouldn't be able to make her cum like this, but he wasn't planning for that.

She was surprised, after the pain of all the pins, he started playing with her pussy. It was slow, but he was rubbing one of the most sensitive parts of her pussy. In fact, it was too slow. She couldn't possibly get anywhere close to cumming like that, and when he started to stroke her clit, she became excited. But again, the speed and movement was infuriatingly slow.

He removed his finger and suddenly she felt an explosion of pain, centred on her clit and radiating out. It was more pain than she had ever felt. She tried escaping, but she was secured quite well. She couldn't move forward or backwards. She was screaming, but the gag was muffling it to a low whine. She caught her breath and the pain still hadn't subsided. In fact, it seemed to have spread, encompassing her entire pussy. She was screaming in short gasps after a few seconds, although the initial pain had now lost it's edge, there was still a persistent sting. Combined with the pain in her breasts, she was on the verge of unconciousness.

Jack had played with her until her clit became hard and stuck out slightly. Then, he placed a clothespin on it. He had never witnessed the kind of struggling that his slut had just shown him. He was afraid that she would rip the hooks out and break the board at the base of the bed. She was trying to scream, and luckily the gag did a good job of blocking that, because certainly the neighbours would have asked questions. He was actually surprised, and for a second, almost removed the pin from the reaction he got. But she calmed, and although still freaking out, she wasn't moving as much and her screaming had reduced. He had taken the opportunity of her distraction to add 3 pins to each labia, with the string through them.

After about 30 seconds, she had stopped screaming and had started sobbing. Her tears were dragging even more of her mascara all over the place. She had already mussed her makeup with her disobedience at the steakhouse, but now the waterworks were causing the black to spread. Drops were hitting the white sheet beneath her and leaving black stains.

He then went back into his bag and pulled out the lube. This is where his plan was going to get him something he wanted from her, the final frontier, if you will. He was going to hurt her, torture her, and he was going to do something she had never thought to let anyone do. He was going to take her anal cherry and he was going to do it with very little regard for her pleasure.

He started by just rubbing some of lube on her asshole. He applied a bit to his index finger, and slowly worked it into her rectum. She started to shake her ass, trying to get away from the probing digit. He slapped her hard on the left ass cheek, leaving a nice red imprint. She seemed to be repeating her unwillingness into her gag. She was even trying to shake her head, as much as her bonds would let her. If she was having such a strong opposition to one finger, he was sure she would hate what was coming next. He had a couple of more preparations to do before he was ready to violate her ass.

After he was sure there was enough lube, he reached into the bag again and pulled out a small butt plug. It had a conical shape, that grew to an inch at it's widest, then closed up and had a small, narrow handle. It was clearly designed to be inserted and extracted repeatedly. He applied some lube to the plug and started to push it in. Her movements didn't abate, and he was getting tired of struggling at the tightness of her anal opening, and also the displacement of his target due to her squirming. He decided nice and easy wasn't going to be enough for this bitch.

"Cunt, I am very very angry. I wanted to do this nice and easy for you, try not to cause you too much discomfort. But it looks like...you...prefer...the hard way!!" He shouted out as he shoved the plug into her ass with full force. At first, it didn't look like it would give, but the constant pressure and the slightly numbing effect of the lube allowed him enough of an opening to slide the tiny toy into her.

She was becoming delirious. The agony in her cunt was still present, and the pinching of her skin was still causing her considerable pain. As if all that wasn't enough, Jack had put something in her ass. Hard. She had never tried anal, and truly, never hoped to. She considered it an exit only. She didn't even think about it when she gave herself to her master. But now, she was frightfully aware of how much control he had, and how little she knew of his intentions. The fear and pain were putting her into a trance. It wasn't simply arousal or sexual craving, but a sense of loss of control that was liberating her. She finally understood her true needs. She now understood that her mind did not crave the freedom of never having to think or make a decision, but rather, her mind wanted to know that it had no control at all. The extreme pain woke her to the realization that her body wasn't hers, and she was happy about it. With this epiphany, she also felt something she didn't think was possible, she felt a climax building in her ass and pussy.

Jack noticed when she relaxed. He didn't expect it, but it was obvious. One moment she was screaming, and the next, she went almost limp. Then, just as quickly, her knees started to shake. He noticed the pins on her labia were vibrating. This he could now recognize was the beginning of her climax. He moved from behind her and climbed onto the bed next to her. He leaned close to her ear.

"You can cum, slut."

And she did. All her climaxes today were not enough to reduce the energy and force of this one. Even Jack was stunned. Her whole body started to convulse. It was for all appearances a seizure. Every muscle in her body would tense, then relax, then tense back up. Over and over, for almost a minute. He hadn't touched her since it started. After a little bit, she finally went fully limp, hanging by the ropes attached to her hands. Her eyes were closed and drool was dripping off her chin from the screaming and moaning. Her breathing was laborious, and every few seconds she would have a tremor. He let her rest for a full 10 minutes while he grabbed a beer and removed all his clothing. He was hard as a rock, the display of her orgasm being something he had never even imagined. He wanted to have his own finish, but he wanted to leave it till the last, and he already knew where he wanted to cum.

After the rest period, he woke her from her unconsciousness.

"Looks like you enjoyed the preliminaries. Shall we get on with the main event?"

She was disoriented from the force of her climax. She wasn't sure what he meant by main event. But after the eureka moment she had and the power of her cum, she would allow him to do anything he wanted.

He pulled the butt plug out of her ass and grabbed another one, slightly longer and only about a half inch thicker. He lubed it up and added a dollop on her brown eye and started to work it in. She had stopped moving, and despite her breathing and grunting indicating it was defenitely hurting, she kept her ass in place and allowed him to make slow progress. This plug was similar in design to the previous one, and once completely inserted, he applied lube around the protruding part and started to saw it in and out. He would keep the bulbous part lodged in her opening for a second, then push back in, then pull it out till only the tip was in, push it back, then pull and hold at the widest. He was training her sphincter to handle the girth of the plug, and after about 30 strokes, he was able to slide it in and out quite easily.

Then he grabbed another, and this would be the last one. This one was as thick as his cock, a full 2 and a half inches. It wasn't nearly as long, but that was on purpose. He wanted to be able to get his cock in, but still make her feel the excruciating pain of a rapid and forced insertion. Jack just didn't want to lose his cock in the process.

After a full 15 minutes with the largest plug, he felt her ass would be ready. If not, too bad. He squirted a bunch of lube in her slightly gaping asshole, then applied some to the head and shaft of his cock. It glistened in the light, as did her ass from all the lube he had used. He rubbed some into her ass cheeks, and then brought his fuck stick to the opening.

She was biting hard into the ball gag. Her asshole was in a lot of pain. She wasn't sure what he was planning, but the 3 plugs he had used had felt so huge that she assumed he planned to fuck her there. She was certain it wouldn't fit, and also had the certainty he would make it. Her apprehension was curbed only by the fact that she now knew that pain was the strongest trigger to her sexual fulfilment, and assumed this would bring about more pleasure than agony.

He lined up his cock head and pushed at the slightly distended opening. Surprisingly, his spongy tip entered her with little resistance. Her sphincter was now used to being open, and he figured the hard part was about to start. He push the first 2 inches of his shaft into her, almost 3 inches total, when he felt the first resistance. It was tight, but not in the same way as a pussy. It was definitely more textured and less accommodating. At the 5 inch mark, when more than half his shaft was inserted into her chocolate starfish, she started cramping. The pain was forcing her to contract her anus and colon, enhancing the pleasure for Jack, but making it difficult to go the rest of the way in. This was not going to work, he thought to himself.

"Slut, you need to relax. Just breathe slowly, through your nose. Focus on the feeling of the air entering your lungs."

She tried to do that, but every breathe brought her more pain from the pins stuck to her breasts and torso. There was no relief. The pain was everywhere. She instead started to focus on the individual points of the pain. She started with her asshole. It felt like it had ripped, and she felt the stretched skin around his warm dick. She focused on it and started to relax her muscles, reducing the cramps. She then tried to open herself, to give her ass to him, and felt another inch slip in. She wanted to tell him to pull back and push in, spreading the lube, but she couldn't with the gag in place. She also couldn't rock back and forth, so she just focused on the next point of pain. Her clit was throbbing in it's vise-like grip. The clothespin would wobble slightly, making sure the pain wouldn't be forgotten. Her pussy lips felt stretched by the weight of the implements. Her nipples were now numb, being in the grips of the laundry aids for almost an hour at this point. The skin on her tits and tummy felt tight, no doubt because so much of it was pinched to accommodate the fasteners.